- Synthesis of Polysubstituted 2-Naphthols by Palladium-Catalyzed Intramolecular Arylation/Aromatization Cascade
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A palladium-catalyzed intramolecular α-arylation and defluorinative aromatization strategy for the synthesis of polysubstituted 2-naphthols is reported. With ortho-bromobenzyl-substituted α-fluoroketones as the substrates and palladium acetate/triphenylphosphine as the catalyst, this method features good functional group tolerance, readily available catalyst and starting materials, and high yields. The applications of the strategy are demonstrated by the synthesis of useful building blocks, such as naphtha[2,3-b]furan, naphthol AS-D, and ligands/catalysts. (Figure presented.).
- Cai, Jinhui,Hu, Xu-Dong,Liu, Wen-Bo,Wang, Zhen-Kai,Yao, Fei,Zhang, Yun-Hao
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- NaHSO4/SiO2catalyzed generation of: o -quinone/ o -thioquinone methides: synthesis of arylxanthenes/ arylthioxanthenes via oxa-6π-electrocyclization
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ortho-Quinone methides, very reactive transient intermediates, are utilized successfully in synthesizing complex organic molecules of natural and biological significance. Among several synthetic protocols, the acid catalyzed generation of ortho-quinone me
- Anthony, Savarimuthu Philip,Karthick, Muthupandi,Konikkara Abi, Edwin,Ramanathan, Chinnasamy Ramaraj,Someshwar, Nagamalla
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supporting information
p. 8653 - 8667
(2020/11/17)
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- De Novo Synthesis of Phenols and Naphthols through Oxidative Cycloaromatization of Dienynes
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In this work, a rhodium-catalyzed oxidative cycloaromatization of dienynes, which provides a highly straightforward and efficient way to access polysubstituted naphthols and phenols under mild conditions, is described. Challenged electron-withdrawing groups are well tolerated in this protocol, and late-stage phenyl ring formation is demonstrated.
- Rong, Ming-Guang,Qin, Tian-Zhu,Liu, Xin-Rui,Wang, Hong-Fa,Zi, Weiwei
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supporting information
p. 6289 - 6293
(2018/10/09)
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- Tunable synthesis of 3-acyl-2-naphthols and 3-substituted isocoumarins via jones reagent promoted cascade reactions of 2-(4-hydroxy-but-1-ynyl) benzaldehydes
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Novel and efficient synthesis of 3-acyl-2-naphthols and 3-substituted isocoumarins via the tunable cascade reactions of 2-(4-hydroxy-but-1-ynyl) benzaldehydes have been developed. Treatment of 2-(4-hydroxy-but-1-ynyl) benzaldehydes with 0.7 equiv of Jones
- He, Yan,Zhang, Xinying,Shen, Nana,Fan, Xuesen
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p. 10178 - 10191
(2013/11/06)
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- Enantioselective oxidative biaryl coupling reactions catalyzed by 1,5-diazadecalin metal complexes: Efficient formation of chiral functionalized BINOL derivatives
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Chiral 1,5-diaza-cis-decalins have been examined as ligands in the enantioselective oxidative biaryl coupling of substituted 2-naphthol derivatives. Under the optimal conditions employing 2.5-10 mol % of a 1,5-diaza-cis-decalin copper(II) catalyst with oxygen as the oxidant, enantioselective couplings (44-96% ee) could be achieved for a range of 3-substituted 2-naphthols including the ester, ketone, phosphonyl, and sulfonyl derivatives. The relationship between the substitution of the naphthalene starting materials and reactivity/selectivity is determined by several factors which act in concert: (1) the effect of substituents on the oxidation potential of the substrate, (2) the ability of the substrate to participate in a chelated copper complex which depends on (a) the inherent coordinating ability of the 3-substituent and (b) substituent steric interactions that affect chelation between the 2-hydroxyl and 3-substituent, (3) the effect of substituents on dissociation of the product from the copper catalyst.
- Li, Xiaolin,Hewgley, J. Brian,Mulrooney, Carol A.,Yang, Jaemoon,Kozlowski, Marisa C.
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p. 5500 - 5511
(2007/10/03)
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- Hypervalent iodine in synthesis 59: Application of polymeric diaryliodonium salts as aryl transfer reagents in SPOS
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Polymeric diaryliodonium salts were employed as aryl transfer reagents in the Pd(II) catalyzed cross-coupling reaction with salicylaldehydes, and could be regenerated and recycled for the same reactions.
- Chen,Chen
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p. 1175 - 1177
(2007/10/03)
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- Effect of cyclodextrin complexation on photo-fries rearrangement of naphthyl esters
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Photolysis of β-cyclodextrin inclusion complexes of 1- and 2-naphthyl esters (acetates and benzoates) in aqueous medium, results in rearrangement to give one isomer of acylnaphthol in excess, whereas the solid state irradiation of the cyclodextrin complexes yields selectively one isomer. In addition, formation of cleavage product is totally suppressed. This remarkable selectivity is attributed to specific modes of the complexation of the esters into the β-CD cavity.
- Banu, Habeeb Shayira,Pitchumani, Kasi,Srinivasan, Chockalingam
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p. 9601 - 9610
(2007/10/03)
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- Photo-Fries reaction of naphthyl esters within zeolites
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Photolysis of naphthyl esters within zeolites leads to the photo-Fries rearrangements as in isotropic solution. However, a high level of product selectivity is obtained using 'cation as the key'. A key component for predicting the selectivity of photoreactions within zeolites, namely the location of reactants, is missing at this stage.
- Pitchumani,Warrier,Cui,Weiss,Ramamurthy
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p. 6251 - 6254
(2007/10/03)
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